CA1296334C - Substituted pyrimidoquinoxalines - Google Patents
Substituted pyrimidoquinoxalinesInfo
- Publication number
- CA1296334C CA1296334C CA000544627A CA544627A CA1296334C CA 1296334 C CA1296334 C CA 1296334C CA 000544627 A CA000544627 A CA 000544627A CA 544627 A CA544627 A CA 544627A CA 1296334 C CA1296334 C CA 1296334C
- Authority
- CA
- Canada
- Prior art keywords
- oxide
- dihydro
- pyrimido
- quinoxaline
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- DBTVBWWMSVATOP-UHFFFAOYSA-N pyrazino[2,3-f]quinazoline Chemical class C1=NC=C2C3=NC=CN=C3C=CC2=N1 DBTVBWWMSVATOP-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- ASOCMUKNAWJETD-UHFFFAOYSA-N 2-ethyl-2-methyl-5-(4-methylphenyl)-6-oxido-8-(trifluoromethyl)-1,3-dihydropyrimido[1,2-a]quinoxalin-6-ium Chemical compound C1C(CC)(C)CN=C2N1C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=C2C1=CC=C(C)C=C1 ASOCMUKNAWJETD-UHFFFAOYSA-N 0.000 claims 3
- CAVVDOSWJKZABH-UHFFFAOYSA-N 2,2-diethyl-6-oxido-5-phenyl-8-(trifluoromethyl)-1,3-dihydropyrimido[1,2-a]quinoxalin-6-ium Chemical compound C1C(CC)(CC)CN=C2N1C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=C2C1=CC=CC=C1 CAVVDOSWJKZABH-UHFFFAOYSA-N 0.000 claims 2
- GJDPRCRWTQKIIL-UHFFFAOYSA-N 2,2-dimethyl-6-oxido-5-phenyl-8-(trifluoromethyl)-1,3-dihydropyrimido[1,2-a]quinoxalin-6-ium Chemical compound C1C(C)(C)CN=C2N1C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=C2C1=CC=CC=C1 GJDPRCRWTQKIIL-UHFFFAOYSA-N 0.000 claims 2
- FKBJUQKMDDUFEC-UHFFFAOYSA-N 6-oxido-5-phenyl-2,2-dipropyl-8-(trifluoromethyl)-1,3-dihydropyrimido[1,2-a]quinoxalin-6-ium Chemical compound C1C(CCC)(CCC)CN=C2N1C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=C2C1=CC=CC=C1 FKBJUQKMDDUFEC-UHFFFAOYSA-N 0.000 claims 2
- NOHZBJACUNKJMI-UHFFFAOYSA-N 9-fluoro-2,2-dimethyl-6-oxido-5-phenyl-1,3-dihydropyrimido[1,2-a]quinoxalin-6-ium Chemical compound C1C(C)(C)CN=C2N1C1=CC(F)=CC=C1[N+]([O-])=C2C1=CC=CC=C1 NOHZBJACUNKJMI-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- FSWKUFNSTOPPEA-UHFFFAOYSA-N 2,2-dimethyl-5-(4-methylphenyl)-6-oxido-8-(trifluoromethyl)-1,3-dihydropyrimido[1,2-a]quinoxalin-6-ium Chemical compound C1=CC(C)=CC=C1C1=[N+]([O-])C2=CC(C(F)(F)F)=CC=C2N2C1=NCC(C)(C)C2 FSWKUFNSTOPPEA-UHFFFAOYSA-N 0.000 claims 1
- OPCQGZFPJAXAOY-UHFFFAOYSA-N 5-(4-fluorophenyl)-2,2-dimethyl-6-oxido-8-(trifluoromethyl)-1,3-dihydropyrimido[1,2-a]quinoxalin-6-ium Chemical compound C1C(C)(C)CN=C2N1C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=C2C1=CC=C(F)C=C1 OPCQGZFPJAXAOY-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 9
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- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 abstract 1
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/897,461 | 1986-08-18 | ||
| US06/897,461 US4758565A (en) | 1986-08-18 | 1986-08-18 | Substituted pyrimidoquinoxalines useful as anti-anaerobic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1296334C true CA1296334C (en) | 1992-02-25 |
Family
ID=25407933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000544627A Expired - Lifetime CA1296334C (en) | 1986-08-18 | 1987-08-14 | Substituted pyrimidoquinoxalines |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4758565A (enrdf_load_stackoverflow) |
| EP (1) | EP0256545B1 (enrdf_load_stackoverflow) |
| JP (1) | JP2566974B2 (enrdf_load_stackoverflow) |
| AT (1) | ATE74604T1 (enrdf_load_stackoverflow) |
| CA (1) | CA1296334C (enrdf_load_stackoverflow) |
| DE (1) | DE3778088D1 (enrdf_load_stackoverflow) |
| ES (1) | ES2032413T3 (enrdf_load_stackoverflow) |
| GR (1) | GR3004321T3 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9114426D0 (en) * | 1991-07-03 | 1991-08-21 | Nat Res Dev | Compounds useful for treating tumours ii |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4472401A (en) * | 1981-11-27 | 1984-09-18 | Roussel Uclaf | Pyrimido-quinoxalines having antiallergic properties |
| US4510143A (en) * | 1982-02-17 | 1985-04-09 | Roussel Uclaf | Antiallergic pyrimido[1,2-a]quinoxalin-2-carboxylic acid derivatives |
| US4696928A (en) * | 1985-09-09 | 1987-09-29 | G. D. Searle & Co. | Substituted dihydroimidazo[1,2-a]quinoxalines |
-
1986
- 1986-08-18 US US06/897,461 patent/US4758565A/en not_active Expired - Lifetime
-
1987
- 1987-08-14 CA CA000544627A patent/CA1296334C/en not_active Expired - Lifetime
- 1987-08-17 ES ES198787111892T patent/ES2032413T3/es not_active Expired - Lifetime
- 1987-08-17 AT AT87111892T patent/ATE74604T1/de not_active IP Right Cessation
- 1987-08-17 JP JP62203972A patent/JP2566974B2/ja not_active Expired - Lifetime
- 1987-08-17 DE DE8787111892T patent/DE3778088D1/de not_active Expired - Fee Related
- 1987-08-17 EP EP87111892A patent/EP0256545B1/en not_active Expired - Lifetime
-
1992
- 1992-04-09 GR GR920400499T patent/GR3004321T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0256545B1 (en) | 1992-04-08 |
| GR3004321T3 (enrdf_load_stackoverflow) | 1993-03-31 |
| ATE74604T1 (de) | 1992-04-15 |
| JP2566974B2 (ja) | 1996-12-25 |
| US4758565A (en) | 1988-07-19 |
| DE3778088D1 (de) | 1992-05-14 |
| EP0256545A1 (en) | 1988-02-24 |
| JPS6399072A (ja) | 1988-04-30 |
| ES2032413T3 (es) | 1993-02-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed | ||
| MKLA | Lapsed |
Effective date: 19990225 |